Evidence suggests that household chaos is associated with less optimal child outcomes. Yet, there is an increasing indication that children’s experiences in childcare may buffer them against the detrimental effects of such environments. Our study aims were to test: (1) whether children’s experiences in childcare mitigated relations between household chaos and children’s cognitive and social development, and (2) whether these (conditional) chaos effects were mediated by links between chaos and executive functioning. Using data from The Family Life Project (n = 1235)-a population-based sample of families from low-income, rural contexts-our findings indicated that household disorganization in early childhood was predictive of worse cognitive and social outcomes at approximately age five. However, these relations were substantially attenuated for children attending greater childcare hours. Subsequent models indicated that the conditional associations between household disorganization and less optimal outcomes at age five were mediated by conditional links between disorganization and less optimal executive functioning.